Vacation rentals with a pool in Cupertino

4.93 out of 5 average rating, 149 reviews

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

CherylynRating, 5 stars1 week ago

We had a wonderful stay at Bill's guest cottage. We found everything as advertised, and the surroundings, especially at sunrise, were serene. The vines were lovely and the morning air fresh and crisp. The beds were very comfortable, and the living space fully accommodated our party of three (two adults, one teenager). We spent most of our daytime out and about with nearby family, so we did not have a chance to try out the kitchen, but it was well-stocked. Bill was highly responsive throughout the booking process and answered our questions. We highly recommend!

4.99 out of 5 average rating, 320 reviews

Guesthouse in Woodside

Rustic Cabin in the Redwoods

DannyRating, 5 stars1 month ago

We will definitely be coming back. It's an amazing escape with beautiful surroundings. The amenities were perfectly curated with even some food items in the refrigerator ready for you when you arrive. I do want to pass on a helpful hint - the road to the home is very curvy and the small road that leads to the entrance of the home is off of the main road and is not obvious if you are not ready and looking for it. You can stay here with confidence knowing that you will have a wonderful experience.

Guesthouse in Monte Sereno

A spacious outdoor area features a glimmering pool set against lush greenery. A patio with comfortable seating and a covered area is visible in the background, providing a place for relaxation. Trees and shrubs frame the scene, adding to the tranquil atmosphere.

4.98 out of 5 average rating, 422 reviews

Quiet Poolside Cottage for Solitude

SheriRating, 5 stars4 weeks ago

Stunning space in a beautiful backyard with gardens and pool. We enjoyed the neighborhood, Los Gatos, Saratoga, lovely dining experiences, wineries, and just exploring. All first class with the help of Marlene's numerous recommendations! What made our stay so special was all that, but more so was our interactions with Marlene. She is a delight and a wonderful host, and we look forward to future visits.

Guest suite in Willow Glen

A tranquil outdoor space features a swimming pool with a built-in hot tub. Surrounding greenery and wooden fencing create a private atmosphere. Light-colored stone detailing and brick accents enhance the pool edge. Lounge chairs are positioned near the water, inviting relaxation.

4.95 out of 5 average rating, 141 reviews

Private Queen Suite-Pool & Hot Tub, private entry

JessicaRating, 5 stars2 weeks ago

Met Todd just after I arrived, very nice & friendly. Asked if there were any problems thus far & very quick to get the hot tub ready for use. Beautiful set up in backyard. And answers back in the app with any questions. I’m local & will definitely be back!

4.94 out of 5 average rating, 139 reviews

Home in Ben Lomond

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

ElizabethRating, 5 stars3 weeks ago

This was the most peaceful and beautiful space I have ever been to. The view from the balcony was gorgeous. All the greenery and the deers and random dog was super gorgeous and felt really at home. The hot tub was amazing and super relaxing. Robert was very kind and responsive, Received a phone call about all the lights, hot tub, close trails, and recommended spots!! Super helpful and very kind gesture. Would 100% go back to this place

4.86 out of 5 average rating, 125 reviews

A sparkling, heated pool occupies the backyard, surrounded by lush greenery and palm trees. Brick edging outlines the pool, enhancing the outdoor space, while a privacy fence adds to the tranquil setting. Sunlight reflects off the water, creating an inviting atmosphere.

Home in San Jose

Beautiful 3BD Home w/ Heated Pool and Fire Pit

BaharehRating, 5 stars13 months ago

The house was great for our family stay. Lots of space, all on one level, and beautiful outdoor space. We travelled with our kids and they had a great time in the pool :) Note there is extra cost if you want the pool to be heated. Thanks for a great stay!

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What guests are saying

Luxurious Ritz Suite w fireplace, Business retreat

4.98 out of 5 average rating, 158 reviews2 weeks ago

Sheryl was a great host & Beautiful place! Amazing spa bathroom with steam shower and jacuzzi gives the perfect spa like ambiance. The little details were perfect. This was my 2nd time staying at the Ritz Suite and would definitely recommend for anyone looking to have a relaxing getaway!

Guest suite in Sunnyvale

What guests are saying

A freestanding casita in a delightful grape garden

4.78 out of 5 average rating, 36 reviews1 month ago

Thank you Maria. We were there for work but had a day off in between. We were planning on spending our day off doing something off property but we were already in the most beautiful place we could imagine. We felt like we were in our own private spa. Pool, Hot Tub, Spectacular flowers, grapevines, dining table on the patio and more outdoor space. The beds were comfortable and the bath & kitchen were both very nice. Hope to come back again and spend more time off at your Casita. Thanks again!!

Guesthouse in Emerald Hills

What guests are saying

Chic two bedroom pool house

4.95 out of 5 average rating, 39 reviews7 months ago

The place is 3 minutes walk to Safeway, Walgreen and Molly Stone. Burlingame Ave full of restaurants and shops with wide sidewalks is right around the corner. We are amazed how convenient this place is. It also has a heated pool and hot tub that our grandkids used a few times. Would love to stay there again. Due to cool weather at night, we love to have the window open at night. It would help if there were a screen even though there were only occasional bugs. Thanks, Anna and Ryan for sharing this jewel of a place.

Guesthouse in Burlingame

What guests are saying

Mission style, w. Pool, Hot tub, walk to downtown

4.89 out of 5 average rating, 54 reviews8 months ago

We stayed at Sara's while visiting family nearby, but her home felt like a vacation in itself. The backyard is magical - we spent a fair amount of time there, swimming, grilling/dining, reading/napping. The backyard (and its myriad diversions) even lured our tech-obsessed teenagers away from their devices for extended periods. Everything was well maintained, no detail overlooked. We also enjoyed the access to a peloton bike and workout equipment. The interior was clean, organized, stylish but comfortable. The sunroom and small courtyard off of the bedrooms were great for yoga or stealing a quiet moment with a cup of coffee or book. Sara was responsive and attentive. Instruction booklet was clear and helpful. The stay exceeded our expectations. We hope to be back.

Home in Menlo Park

What guests are saying

Beautiful Entire Home | Bay Views | Private Pool

4.91 out of 5 average rating, 70 reviews4 weeks ago

Nelson’s place was very nice, and was one of few places available with a pool, in a reasonable and competitive price range. Although they were dated and showing some wear, the furnishings were comfortable, and the space was adequately equipped to prepare and serve meals. The location was convenient, felt safe and offered great views. We enjoyed our time here and felt that the price fairly represented the space, reasonable, comfortable, safe, and fun.

Home in South San Francisco

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Popular amenities for Cupertino rentals with a pool

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Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 5 reviews

An overhead view of the living space shows a foosball table beside a light-colored sectional sofa. A chandelier hangs from the ceiling, illuminating the room. An entertainment unit and decorative artwork provide a welcoming touch to the open layout.

Home in Santa Clara

Retreat @ Oasis Pool/Hot Tub/Billiards/Game SF Bay

SharynRating, 5 stars1 month ago

I booked this home for my colleagues from overseas, and they had a fantastic stay. The host was highly professional and responsive, promptly addressing all requests and ensuring everyone’s comfort throughout their visit. Their attentiveness made the experience seamless and enjoyable. Highly recommended!

4.92 out of 5 average rating, 64 reviews

A clear swimming pool reflects sunlight, accompanied by a small rock waterfall. A tree is positioned nearby, adding a touch of greenery. The outdoor space features lounge seating and a BBQ grill under a roofed area, allowing for shade and comfort.

Home in Felton

Redwood Oasis - Private Heated Pool by State Park!

Victoria And JasonRating, 5 stars4 months ago

Everything about our stay was fantastic!! The beds, the pool, the town…the three of us loved this Airbnb and look forward to coming back. Swimming in a heated pool in the winter is a heavenly experience.

4.91 out of 5 average rating, 11 reviews

A bright sunroom features large glass windows that invite natural light. A comfortable dark chair and a small circular table are positioned on terracotta tiles, while exposed brick walls add texture. Two doors lead to the outside, enhancing the view and accessibility.

Home in Atherton

Home in Atherton, Menlo Park

ChelseaRating, 5 stars1 month ago

Feng’s home was lovely and very spacious! We had a group of 8 guests staying and it could accommodate a larger group very well! Thank you for a lovely accommodation, Feng!

4.84 out of 5 average rating, 44 reviews

A serene swimming pool is surrounded by a natural stone border, with a built-in jacuzzi featuring a circular step design. The clear water reflects sunlight, creating a tranquil atmosphere. Poolside lounge chairs and a sheltered seating area are visible in the background.

Home in San Jose

Perfect home with pool for family vacations!

DaveRating, 5 stars7 months ago

Such a nice place to stay in Silicon Valley. Tucked back into the beautiful hills, with a walking loop through the oak trees just down the street. Responsive host. A perfect retreat.

4.95 out of 5 average rating, 78 reviews

An outdoor area features a solar-heated fenced-in pool surrounded by tall green hedges. A shaded seating area is visible under a canopy, with a gas grill and storage cover nearby. The patio is designed with textured concrete, providing a spacious environment for relaxation.

Home in Campbell

Luxury 4-Suite Carbon-Neutral Home With Pool

ChiRating, 5 stars3 weeks ago

Dan was a great host! He was quick to respond to any questions/concerns during the stay. We actually had a hiccup or two during the stay, and he was prompt to fix the issues by having someone come over to resolve them within 2 hours. The home is beautiful and spacious and has basically all your kitchen needs, so that's always great to have! 10/10 recommend

4.88 out of 5 average rating, 25 reviews

A lush backyard features a swimming pool surrounded by lounging chairs under a large umbrella. Palm trees and flowering plants enhance the tropical feel, while a wooden fence provides privacy. Clear blue skies and gentle clouds complete the serene outdoor setting.

Home in Felton

Tropical Felton Oasis

KristyRating, 5 stars2 weeks ago

Great stay in Felton! The location was perfect, peaceful and scenic, yet just a short drive to Santa Cruz. The house was clean and comfortable, and Jessica was fantastic host. She was easy to communicate with and gave us some great local recommendations. Would definitely stay here again!

4.94 out of 5 average rating, 358 reviews

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Silicon Valley Luxury I Sauna, Hot Tub, Pool

YiRating, 5 stars1 week ago

Very beautiful place, nothing to complain, we enjoy it.

4.84 out of 5 average rating, 57 reviews

A refreshing swimming pool is framed by lush greenery and bordered by a clean patio area. Two lounge chairs are positioned nearby, inviting relaxation. Sunlight reflects off the water, creating a calming atmosphere suitable for unwinding or enjoying time with family.

Home in Hayward

The Happy Hideaway - Pool, enjoyable backyard!

TheebaRating, 5 stars1 day ago

wonderful host - very proactive and excellent communication. Thank you for being such a great host!

Show all

Condo rentals with a pool

A comfortable living area features a light-colored couch and a chic glass coffee table atop an area rug with abstract patterns. Large windows with sheer curtains provide natural light and lead to a small outdoor balcony overlooking greenery.

Condo in Santa Clara

4.88 out of 5 average rating, 17 reviews

Luxurious 2 bed 2 bath Condo in Santa Clara, CA

BharathRating, 5 stars4 months ago

I had an incredible experience staying at Kitty’s place! The home was cozy, and the location was perfect. The host was super responsive and went above and beyond to make sure I had everything I needed. I wouldn’t hesitate to book this place again. Thank you for a fantastic stay!

4.67 out of 5 average rating, 3 reviews

The exterior of the townhouse features a landscaped front yard with low-maintenance greenery, including shrubs and small trees. A concrete pathway leads to the blue front door, framed by an adjacent wooden fence. The two-story structure presents a modern design with a neutral color palette.

Condo in San Jose

Charming 1 bedroom, 1 bath, 2 Story Condo.

TomRating, 5 stars10 months ago

Everything was great! The unit had everything you could possibly need for a trip (stocked bathroom, stocked kitchen, tons of extra towels and blankets). The neighborhood was also very quiet, which was great because we're light sleepers. I would definitely recommend this spot and would stay again.

5 out of 5 average rating, 17 reviews

An outdoor pool area features a spacious swimming pool surrounded by lounge chairs. Tall trees provide shade in the background, and a clubhouse is visible nearby. A clean, paved patio area completes the setting, inviting relaxation and leisure.

Condo in Willow Glen

Stylish Silicon Valley Retreat – Perfectly Located

GaryRating, 5 stars3 months ago

Great host- from the time we booked the Airbnb until the time we signed out (and after), Kwesi was always available, and genuinely interested in how we were doing G, what else we might need, etc. Great place- clean, quiet, beautiful, nice location.

4.63 out of 5 average rating, 19 reviews

An outdoor swimming pool is surrounded by a sunlit patio. Lounge chairs are positioned along the pool's edge, providing space for relaxation. Towering trees offer shade in the background, while a building features large windows overlooking the area.

Condo in Mountain View

Lovely 1B1B condo with patio near downtown MTV

DavidRating, 5 stars2 weeks ago

Excellent place to stay. Fantastic host. Great value. Enjoyed our stay and would be back to stay again.

An outdoor swimming pool and hot tub are surrounded by several lounge chairs and umbrellas. A garden area with greenery encircles the pool. The building's exterior, with light-colored walls and terracotta roof tiles, is visible in the background.

Condo in Palo Alto

4.83 out of 5 average rating, 12 reviews

Contemporary 2BR - Blocks from Stanford Campus

AndreaRating, 5 stars79 months ago

The apartment is placed in a perfect position. You can find everything you need in a walking distance like a supermarket, good places to grab something to eat and gyms. the check-in was easy and perfectly matched the description Dee provided me before the arrival. The house is very spacious and the kitchen fully equipped. I recommend this place for a comfy stay in Palo Alto.

A light-filled living area features a spacious white couch arranged around a round coffee table. A wooden dining table is visible in the background, surrounded by chairs. Large windows provide a view of the greenery outside, and floral wallpaper adds a decorative touch.

Condo in San Jose

4.8 out of 5 average rating, 25 reviews

Luxe 2Bed/2Bath w/ Parking, Fast WiFi, Pool & Gym

JimRating, 5 stars2 weeks ago

Great place, comfy, and felt like a home. The location was easily accessible to major roadways which made driving very easy. With a host who was very responsive and clear, there was nothing else that I would ask for out of a vacation stay.

4.89 out of 5 average rating, 9 reviews

A spacious living area is visible, featuring a large black leather couch and a wooden coffee table. A soft rug lies under the seating area. A dining table can be seen in the adjacent room, complemented by warm wood flooring and ample natural light from nearby windows.

Condo in Menlo Park

Willow Place

SiavashRating, 5 stars1 month ago

Ryan is a great host answered all of our questions, addressed our requests/needs promptly. A neat safe place near shopping and close to Stanford university met our goal of staying in the area.